4.7 Article

Thioarylative Radical Cyclization of Yne-Dienone

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JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 16, 页码 10509-10517

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01445

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  1. CEFIPRA [5505-2]
  2. DST India
  3. UGC
  4. CSIR

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We herein demonstrated a N-hydroxyphthalimide (NHPI)-mediated chemo- and regioselective radical cyclization of yne-dienone with thiols to construct 3-thioaryl bearing [6,6]-fused dihydrochromenone derivatives. This transformation tolerates common functional groups and has broad scope. The reaction proceeds via the attack of a thioaryl radical to alkyne over the activated Michael acceptor. The TEMPO quenching experiment suggests the involvement of a radical intermediate. Synthetic versatility of 3-thioaryldihydrochromenones is also showcased.

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